Trifluoroacetic acid → HCID 178519146, compound

HRID 539123Notes

Reaction equation

HRID 539123 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:12][O:11][C:10](=[O:13])[N:9]2[C:14]2[CH:19]=[CH:18][N:17]3[N:20]=[CH:21][C:22]([C:23]4[CH:28]=[CH:27][C:26]([C:29]5[CH:33]=[CH:32][N:31](COCC[Si](C)(C)C)[N:30]=5)=[CH:25][CH:24]=4)=[C:16]3[N:15]=2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:31]1[CH:32]=[CH:33][C:29]([C:26]2[CH:25]=[CH:24][C:23]([C:22]3[CH:21]=[N:20][N:17]4[CH:18]=[CH:19][C:14]([N:9]5[C@@H:8]([C:5]6[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=6)[CH2:12][O:11][C:10]5=[O:13])=[N:15][C:16]=34)=[CH:28][CH:27]=2)=[N:30]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67034549HCID 67034549, compound

Product 1

HCID 178519146HCID 178519146, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (S)-4-(4-fluorophenyl)-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one (80 mg, 0.14 mmol) in DCM (4 mL) was added TFA (1 mL) and the reaction was stirred for 4 hours at ambient temperature. The reaction was concentrated to dryness, and 7N ammonia in methanol was added to the residue. After concentration to dryness, the residue was purified by reverse phase chromatography (SP4, 12M, water/CH3CN 100:0 to 0:100, 20 column volumes) to yield (S)-3-(3-(4-(1H-pyrazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(4-fluorophenyl)oxazolidin-2-one (35 mg, 57% yield) as a white solid. LCMS (APCI+) m/z 441.2 [M+H]+.

Workup

  1. concentrationThe reaction was concentrated to dryness, and 7N ammonia in methanol
  2. additionwas added to the residue
  3. concentrationAfter concentration to dryness
  4. customthe residue was purified by reverse phase chromatography (SP4, 12M, water/CH3CN 100:0 to 0:100, 20 column volumes)

Sources & evidence

ORD record
ord-08e66353151b4ee588884771ceb6e03f
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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